2021/12/16 更新

写真a

サワダ ダイスケ
澤田 大介
SAWADA Daisuke
所属
医歯薬学域 教授
職名
教授
外部リンク

学位

  • 博士(薬学) ( 東京大学 )

研究キーワード

  • 機能性分子

  • 有機金属化学

  • 医薬化学

  • 全合成

  • Organic Chemisty

  • 有機化学

研究分野

  • ライフサイエンス / 生物有機化学

  • ライフサイエンス / 薬系化学、創薬科学

  • ナノテク・材料 / 構造有機化学、物理有機化学

経歴

  • 岡山大学   大学院医歯薬学総合研究科   教授

    2013年10月 - 現在

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  • 帝京大学   薬学部   准教授

    2010年4月 - 2013年9月

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  • 帝京大学   薬学部   講師

    2006年6月 - 2010年3月

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  • 帝京大学   薬学部   助手

    2001年4月 - 2006年5月

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  • 東京大学   Graduate School of Pharmaceutical Sciences

    2000年 - 2001年

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所属学協会

 

論文

  • Synthesis of α-substituted indolylacetamide using acetonitriles as acetamide enolate equivalents through O-transfer reactions. 国際誌

    Takumi Abe, Kenta Noda, Daisuke Sawada

    Chemical communications (Cambridge, England)   57 ( 61 )   7493 - 7496   2021年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    We introduce readily available ammonium hemiaminals as O-transfer reagents and commercially available acetonitriles as a primary amide enolate precursor. The combination serves as an amide enolate equivalent, thereby providing one-pot access to α-substituted indolylacetamides. A broad substrate scope and good functional group tolerance as well as gram-scale synthesis make this protocol highly attractive. Mechanistic experiments suggest that the cyano group is trapped by a hydroxy group of hemiaminals en route to the desired primary amides under metal-free conditions.

    DOI: 10.1039/d1cc02821a

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  • Morpholine-Substituted Rhodamine Analog with Multi-Configurational Switches for Optical Sensing of pH Gradient under Extreme Acidic Environments. 国際誌

    Natsumi Koga, Masaru Tanioka, Shinichiro Kamino, Daisuke Sawada

    Chemistry (Weinheim an der Bergstrasse, Germany)   27 ( 11 )   3761 - 3765   2020年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    Superior pH-responsive molecules are required for the development of functional materials applicable to advanced molecular technologies. Despite having been widely developed, many rhodamine-based pH-responsive molecules exhibit a single configurational switch for "turn-on." Herein, we report a new type of rhodamine-based pH-responsive molecule with multi-configurational switches displaying stable two-step structural and color conversion in response to pH. This rhodamine analog could be successfully applied to optical sensing of pH gradient under extreme acidic environments both in solution and on hydrogel through high-contrast color change. We demonstrated that this multi-responsive character enabled optical memory of different pH information.

    DOI: 10.1002/chem.202004254

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  • Stepwise structural and fluorescent colour conversion in rhodamine analogues based on light and acid stimulations

    Masaru Tanioka, Shinichiro Kamino, Natsumi Koga, Daisuke Sawada

    JOURNAL OF MATERIALS CHEMISTRY C   8 ( 2 )   543 - 549   2020年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    The research and development of multi-stimuli, multi-responsive molecules have attracted considerable attention in chemistry, biology, and material science. Herein, we propose a multi-stimuli-responsive multi-fluorescence system in a single molecule. This system is based on the isomerization that involves ring-opening/closing reactions of spirolactones of rhodamine analogues (ABPXs), developed by our group, which can be independently controlled by light and chemical stimuli. UV light irradiation opens one of the spirolactones to give thermally stable coloured isomer (Z) in solution. Detailed synthetic and theoretical investigations reveal that the ring-opening reaction of ABPXs proceeds via the formation of a photo-induced charge separated state, followed by the recombination of the biradicals. Furthermore, we explore the structure-kinetic relationships and demonstrate that the introduction of electron-donating substituents into the xanthene ring can tune the lifetime of the photo-generated isomer. Chemical stimulation by an acid further promotes the ring-opening reaction to give a red-shifted isomer (D). These light and chemical input signals can be converted into output signals of distinct colour and fluorescence. The multi-stimuli-responsive multi-colour fluorescence could be distinctively expressed through the combinatorial logic gate.

    DOI: 10.1039/c9tc05054j

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  • Efficient and practical synthesis of N-acetyl enamides from ketoximes by unique iron catalytic system

    Takahiro Kunishige, Daisuke Sawada

    TETRAHEDRON LETTERS   60 ( 24 )   1562 - 1565   2019年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    A new procedure for the iron-catalyzed synthesis of enamides from ketoximes was developed, and its mechanism was proposed. A unique reduction system, with the concerted use of KI and Na2S2O4, was involved. The reaction exhibited a wide substrate scope and gave good yields in a short reaction time. The procedure is operationally simple and also applicable for the large-scale synthesis. (C) 2019 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2019.05.006

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  • Syntheses and acid-stimulus responsiveness of aminobenzopyranoxanthene spiroethers

    Ryosuke Hosoda, Shinichiro Kamino, Masashi Ueda, Daisuke Sawada

    Heterocycles   99 ( 2 )   820 - 824   2019年

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    掲載種別:研究論文(学術雑誌)  

    Novel aminobenzopyranoxanthene spiroethers (ABPX-SEs) based on the spirocyclization of the hydroxymethyl group were synthesized from ABPX spirolactones (ABPX-SLs). The addition of an acid induces a ring-opening reaction to yield two colored monocationic and dicationic spiro-ring species of ABPX. The acid-stimulus responsiveness of the ABPX-SEs is lower than that of ABPX-SLs in polar organic solvents. In addition, the ABPX-SEs exhibit stepwise structural changes of the three equilibrium species at acidic pH, although rapid conversion from the spirolactone to dicationic species occurs in the case of ABPX-SLs.

    DOI: 10.3987/COM-18-S(F)66

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  • Synthesis of a tetracyclic aminobenzimidazole derivative via tandem cyclization of triphenylguanidine

    Yuki Akamatsu, Shinichiro Kamino, Daisuke Sawada

    Heterocycles   99 ( 2 )   815 - 819   2019年

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    掲載種別:研究論文(学術雑誌)  

    We developed a new reaction for the one-pot synthesis of a fused cyclic compound from triphenylguanidine, which was thought to be tandem cyclization, with a moderate yield. In this reaction, conditions such as the metal reagent, oxidant, solvent, and ligand affected whether single or tandem cyclization was preferred.

    DOI: 10.3987/COM-18-S(F)61

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  • Stable Thiele's Hydrocarbon Derivatives Exhibiting Near-Infrared Absorption/Emission and Two-Step Electrochromism. 国際誌

    Yuta Okamoto, Masaru Tanioka, Atsuya Muranaka, Kazunori Miyamoto, Tetsuya Aoyama, Xingmei Ouyang, Shinichiro Kamino, Daisuke Sawada, Masanobu Uchiyama

    Journal of the American Chemical Society   140 ( 51 )   17857 - 17861   2018年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    We report synthesis and characterization of near-infrared (NIR)-absorbing/emitting Thiele's hydrocarbon derivatives, in which four aryl groups are bridged to a quinodimethane skeleton. The quinoid structure of the bridged-tetra-aryl- p-quinodimethanes (BTAQs) was confirmed by spectroscopic, X-ray crystallographic, and computational methods. Although quinodimethane derivatives with a small HOMO-LUMO energy gap often exhibit biradical character, BTAQs showed no biradical character. Instead, they exhibited two-step near-infrared electrochromism. The donor/acceptor properties of the aryl groups were found to play a key role in the unique properties of BTAQs.

    DOI: 10.1021/jacs.8b11092

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  • Effects of 2-substitution on 14-epi-19-nortachysterol-mediated biological events: Based on synthesis and X-ray co-crystallographic analysis with human vitamin D receptor 査読

    Daisuke Sawada, Shinji Kakuda, Akiko Takeuchi, Fumihiro Kawagoe, Midori Takimoto-Kamimura, Atsushi Kittaka

    Org. Biomol. Chem. doi: 10.1039/C8OB00158H   16 ( 14 )   2448 - 2455   2018年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1039/c8ob00158h

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  • Synthesis of Aminobenzopyranoxanthenes with Nitrogen-Containing Fused Rings 査読

    Natsumi Fukino, Shinichiro Kamino, Minami Takahashi, Daisuke Sawada

    JOURNAL OF ORGANIC CHEMISTRY   82 ( 24 )   13626 - 13631   2017年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    An efficient and practical method for the synthesis of a variety of aminobenzopyranoxanthenes (ABPXs) with different nitrogen containing fused rings was developed. On the basis of the mechanistic studies of the formation of the xanthene framework, the presented methodology was developed to facilitate access to previously inaccessible asymmetric ABPXs.

    DOI: 10.1021/acs.joc.7b02290

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  • Direct C-H substitution reaction of anilides using hypervalent iodine and their regioselective issues 査読

    Kohki Yamamoto, Shinichiro Kamino, Daisuke Sawada

    TETRAHEDRON LETTERS   58 ( 41 )   3936 - 3938   2017年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    The direct C-H substitution reactions of anilides using hypervalent iodine proceeded to afford azide, chloro, bromo, and fluoro derivatives, and their regioselectivity were described. In the specific reaction conditions, the unique regioisomers were obtained. (C) 2017 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2017.08.079

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  • Synthesis of 2- and 2-(3-hydroxypropyl)-7,8-cis-14-epi-1,25-dihydroxy-19-norvitamin D3 and their biological activity 査読

    Daisuke Sawada, Eiji Ochiai, Akiko Takeuchi, Shinji Kakuda, Midori Kamimura-Takimoto, Fumihiro Kawagoe, Atsushi Kittaka

    J. Steroid Biochem. Mol. Biol.   173   79 - 82   2017年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1016/j.jsbmb.2016.09.007

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  • Novel screening system for high-affinity ligand of heredity vitamin D-resistant rickets-associated vitamin D receptor mutant R274L using bioluminescent sensor 査読

    Hiroki Mano, Miyu Nishikawa, Kaori Yasuda, Shinichi Ikushiro, Nozomi Saito, Daisuke Sawada, Shinobu Honzawa, Masashi Takano, Atsushi Kittaka, Toshiyuki Sakaki

    JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY   167   61 - 66   2017年3月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Hereditary vitamin D-resistant rickets (HVDRR) is caused by mutations in the vitamin D receptor (VDR) gene. Arg274 located in the ligand binding domain (LBD) of VDR is responsible for anchoring 1 alpha,25-dihydroxyvitamin D3 (1 alpha,25(OH)(2)D-3) by forming a hydrogen bond with the 1 alpha-hydroxyl group of 1 alpha,25(OH)(2)D-3. The Arg274Leu (R274L) mutation identified in patients with HVDRR causes a 1000-fold decrease in the affinity for 1 alpha,25(OH)(2)D-3, and dramatically reduces vitamin D-related gene expression. Recently, we successfully constructed fusion proteins consisting of split-luciferase and LBD of the VDR. The chimeric protein LucC-LBD-LucN, which displays the C-terminal domain of luciferase (LucC) at its N-terminus, can detect and discriminate between VDR agonists and antagonists. The LucC-LBD (R274L)LucN was constructed to screen high-affinity ligands for the mutant VDR (R274L). Of the 33 vitamin D analogs, 5 showed much higher affinities for the mutant VDR (R274L) than la,25(OH)2D3, and 2 alpha-[2-(tetrazol-2-ypethy1]-1 alpha,25-(OH)(2)D-3 showed the highest affinity. These compounds might be potential therapeutics for HVDRR caused by the mutant VDR (R274L). (C) 2016 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.jsbmb.2016.11.008

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  • Water-tunable solvatochromic and nanoaggregate fluorescence: dual colour visualisation and quantification of trace water in tetrahydrofuran 査読

    Masaru Tanioka, Shinichiro Kamino, Atsuya Muranaka, Yoshinao Shirasaki, Yousuke Ooyama, Masashi Ueda, Masanobu Uchiyama, Shuichi Enomoto, Daisuke Sawada

    PHYSICAL CHEMISTRY CHEMICAL PHYSICS   19 ( 2 )   1209 - 1216   2017年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:ROYAL SOC CHEMISTRY  

    While investigating the unique optical properties of aminobenzopyranoxanthenes (ABPXs), organic fluorescent dyes with the fusion of two rhodamines, we have found that the spirolactone form of ABPXs exhibited solvatochromic fluorescence in organic solvents. Detailed spectrophotometric and theoretical analyses showed that the solvatochromic fluorescence of ABPXs originated from the photo-excited charge separation in solvents of different dipolarities. Further studies revealed that fluorescent nano-aggregates were also formed in highly concentrated solution. The intriguing dual fluorescence properties of ABPXs were tunable in response to the water content, and served as a new detection principle for naked-eye visualisation (above 0.5 wt%) and quantification (0.010-0.125 wt%) of water in tetrahydrofuran.

    DOI: 10.1039/c6cp06808a

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  • SYNTHESES AND PHOTOPHYSICAL PROPERTIES OF AMINOBENZOPYRANOXANTHENE DYES CONTAINING VARIOUS ALKYL CHAINS AT AMINE MOIETIES 査読

    Shinichiro Kamino, Masaru Tanioka, Daisuke Sawada, Shuichi Enomoto

    HETEROCYCLES   95 ( 2 )   1167 - 1176   2017年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Aminobenzopyranoxanthene (ABPX) dyes containing linear n-alkyl chains at amino groups were synthesized, and their cis and trans stereoisomers were isolated. Detailed spectrophotometric studies revealed that all the ABPX derivatives exhibited fluorescence emission in the far-red and near-infrared wavelength regions, and their fluorescence quantum efficiency increased with increasing n-alkyl chain length. Almost no differences in photophysical properties were observed between the cis and trans stereoisomers.

    DOI: 10.3987/COM-16-S(S)65

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  • Fused-Fluoran Leuco Dyes with Large Color-Change Derived from Two-Step Equilibrium: iso-Aminobenzopyranoxanthenes 査読

    Yoshinao Shirasaki, Yuta Okamoto, Atsuya Muranaka, Shinichiro Kamino, Daisuke Sawada, Daisuke Hashizume, Masanobu Uchiyama

    JOURNAL OF ORGANIC CHEMISTRY   81 ( 23 )   12046 - 12051   2016年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Fluorans are popular leuco dyes that are used in various applications, such as carbonless-copy papers and thermal papers. Here, we describe unique leuco dyes in which two fluoran units are fused into a C-2h structure (iso-aminobenzopyranoxanthenes; iso-ABPXs). iso-ABPXs exhibited a large two-step color change (colorless/pink and pink/blue-green) due to opening closing of two spirolactone rings. The two-step equilibrium among the colorless, pink, and blue-green forms could be well controlled by adjusting acid concentration, solvent, and/or temperature.

    DOI: 10.1021/acs.joc.6b02403

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  • Revisiting the 7,8-cis-vitamin D3 derivatives: synthesis, evaluating the biological activity, and study of the binding configuration 査読

    Daisuke Sawada, Shinji Kakuda, Midori Kamimura-Takimoto, Akiko Takeuchi, Yotaro Matsumoto, Atsushi Kittaka

    Tetrahedron   72 ( 22 )   2838 - 2848   2016年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1016/j.tet.2016.03.081

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  • Reversible Near-Infrared/Blue Mechanofluorochromism of Aminobenzopyranoxanthene 査読

    Masaru Tanioka, Shinichiro Kamino, Atsuya Muranaka, Yousuke Ooyama, Hiromi Ota, Yoshinao Shirasaki, Jun Horigome, Masashi Ueda, Masanobu Uchiyama, Daisuke Sawada, Shuichi Enomoto

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   137 ( 20 )   6436 - 6439   2015年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Mechanochromic organic molecules (MOMs) that exhibit a large difference of fluorescence wavelength between two states have important potential applications, but few such compounds are known. Here, we report a new MOM, cis-ABPX01(0), which shows switchable near-IR and blue fluorescence responses. Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion between the two molecular packing arrangements in response to mechanical grinding and solvent vapor-fuming.

    DOI: 10.1021/jacs.5b00877

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  • Synthesis and metabolic studies of 1α,2α,25-, 1α,4α,25- and 1α,4β,25-trihydroxyvitamin D3 査読

    Masashi Takano, Daisuke Sawada, Kaori Yasuda, Miyu Nishikawa, Akiko Takeuchi, Ken-ichiro Takagi, Kyohei Horie, G. Satyanarayana Reddy, Tai C. Chen, Toshiyuki Sakaki, Atsushi Kittaka

    J. Steroid Biochem. Mol. Biol.   148   34 - 37   2015年4月

  • ビタミンD受容体リガンドの創製 招待

    橘高敦史, 澤田大介

    ファルマシア   51 ( 3 )   196 - 200   2015年3月

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    記述言語:日本語   掲載種別:研究論文(学術雑誌)  

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  • Synthesis and Preliminary Biological Evaluation of 2-[3-(Tetrazolyl)propyl]-1α,25-dihydroxy-19-norvitamin D3 招待 査読

    Masashi Takano, Erika Higuchi, Kazunari Higashi, Keisuke Hirano, Akiko Takeuchi, Daisuke Sawada, Atsushi Kittaka

    Heterocycles   90 ( 2 )   1274 - 1287   2015年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.3987/COM-14-S(K)108

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  • Synthesis and properties of 14-epi-1α,25-dihydroxy-19-nortachysterol and its 2-substituted derivatives 招待 査読

    Daisuke Sawada, Atsushi Kittaka

    Current Topics in Medicinal Chemistry 2014, 14 (21), 2454-2459.   14 ( 21 )   2454 - 2459   2014年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.2174/1568026615666141208103741

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  • Design and synthesis of 2α-(tetrazolylethyl)-1α,25-dihydroxyvitamin D3 as a high affinity ligand for vitamin D receptor. 査読

    Matsuo M, Hasegawa A, Takano M, Saito H, Kakuda S, Takagi K, Ochiai E, Horie K, Takimoto-Kamimura M, Takenouchi K, Sawada D, Kittaka A

    The Journal of steroid biochemistry and molecular biology   144PA ( PART A )   201 - 203   2014年10月

  • Synthesis and biological activity of 1α,2α,25-trihydroxyvitamin D3: active metabolite of 2α-(3-hydroxypropoxy)-1α,25-dihydroxyvitamin D3 by human CYP3A4. 査読

    Takano M, Ohya S, Yasuda K, Nishikawa M, Takeuchi A, Sawada D, Sakaki T, Kittaka A

    Chemical & pharmaceutical bulletin   62 ( 2 )   182 - 184   2014年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:2  

    DOI: 10.1248/cpb.c13-00646

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  • Synthesis of 2α-heteroarylalkyl active vitamin d3 with therapeutic effect on enhancing bone mineral density in vivo. 査読

    Matsuo M, Hasegawa A, Takano M, Saito H, Kakuda S, Chida T, Takagi K, Ochiai E, Horie K, Harada Y, Takimoto-Kamimura M, Takenouchi K, Sawada D, Kittaka A

    ACS medicinal chemistry letters   4 ( 7 )   671 - 674   2013年7月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:7  

    DOI: 10.1021/ml400098w

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  • Synthesis of 14-epi-2α-hydroxypropoxy-1α,25-dihydroxy-19-nortachysterol and its hVDR binding. 査読

    Sawada D, Tsukuda Y, Saito H, Takagi K, Kakuda S, Takimoto-Kamimura M, Ochiai E, Takenouchi K, Kittaka A

    The Journal of steroid biochemistry and molecular biology   136 ( 1 )   27 - 29   2013年7月

  • Potent 19-norvitamin D analogs for prostate and liver cancer therapy. 査読

    Kittaka A, Yoshida A, Chiang KC, Takano M, Sawada D, Sakaki T, Chen TC

    Future medicinal chemistry   4 ( 16 )   2049 - 2065   2012年10月

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    記述言語:英語   出版者・発行元:16  

    DOI: 10.4155/fmc.12.130

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  • C15-functionalized 16-ene-1α,25-dihydroxyvitamin D3 is a new vitamin D analog with unique biological properties. 査読

    Kumagai G, Takano M, Shindo K, Sawada D, Saito N, Saito H, Kakuda S, Takagi K, Takimoto-Kamimura M, Takenouchi K, Chen TC, Kittaka A

    Anticancer research   32 ( 1 )   311 - 317   2012年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:1  

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  • The difference between 14-epi-previtamin D3 and 14-epi-19-norprevitamin D3: their synthesis and binding affinity for human VDR. 査読

    Sawada D, Katayama T, Tsukuda Y, Saito N, Saito H, Kakuda S, Takimoto-Kamimura M, Takenouchi K, Kittaka A

    Anticancer research   32 ( 1 )   319 - 326   2012年1月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:1  

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  • Synthesis and biological activities of 1α,4α,25- and 1α,4β,25-trihydroxyvitamin D(3) and their metabolism by human CYP24A1 and UDP-glucuronosyltransferase. 査読

    Sawada D, Tsukuda Y, Yasuda K, Sakaki T, Saito H, Takagi K, Takenouchi K, Chen TC, Reddy GS, Kittaka A

    Chemical & pharmaceutical bulletin   60 ( 10 )   1343 - 1346   2012年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:10  

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  • A Multivalent Probe for AI-2 Quorum-Sensing Receptors 査読

    Amanda L. Garner, Junguk Park, Joseph S. Zakhari, Colin A. Lowery, Anjali Kumari Struss, Daisuke Sawada, Gunnar F. Kaufmann, Kim D. Janda

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   133 ( 40 )   15934 - 15937   2011年10月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Multivalency is a common principle in the recognition of cellular receptors, and multivalent agonists and antagonists have played a major role in understanding mammalian cell receptor biology. The study of bacterial cell receptors using similar approaches, however, has lagged behind. Herein we describe our efforts toward the development of a dendrimer-based multivalent probe for studying AI-2 quorum-sensing receptors. From these studies, we have discovered a chemical probe specific for Lsr-type AI-2 quorum-sensing receptors with the potential for enabling the identification of new bacterial species that utilize AI-2 as a quorum-sensing signaling molecule.

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  • New C15-substituted active vitamin D3. 査読

    Shindo K, Kumagai G, Takano M, Sawada D, Saito N, Saito H, Kakuda S, Takagi K, Ochiai E, Horie K, Takimoto-Kamimura M, Ishizuka S, Takenouchi K, Kittaka A

    Organic letters   13 ( 11 )   2852 - 2855   2011年6月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:11  

    DOI: 10.1021/ol200828s

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  • Development of 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor 査読

    Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Shinji Kakuda, Midori Takimoto-Kamimura, Eiji Ochiai, Kazuya Takenouchi, Atsushi Kittaka

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   133 ( 18 )   7215 - 7221   2011年5月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    In the study of the synthesis of 14-epi-19-norprevitamin D-3, we found 14-epi-19-nortachysterol derivatives through C6,7-cis/trans isomerization. We also succeeded in their chemical synthesis and revealed their marked stability and potent VDR binding affinity. To the best of our knowledge, this is the first isolation of stable tachysterol analogues. Surprisingly, 14-epi-19-nortachysterol derivatives exhibited an unprecedented binding configurations for the ligand binding pocket in hVDR, C5,6-s-trans and C7,8-s-trans triene configurations, which were opposite the natural C7,8-ene-configuration of 1 alpha,25(OH)(2)D-3.

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  • Medicinal Chemistry as a Conduit for the Modulation of Quorum Sensing 査読

    Colin A. Lowery, Nicholas T. Salzameda, Daisuke Sawada, Gunnar F. Kaufmann, Kim D. Janda

    JOURNAL OF MEDICINAL CHEMISTRY   53 ( 21 )   7467 - 7489   2010年11月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/jm901742e

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  • Synthesis of 2- and 2-Substituted-14-epi-previtamin D3 and Their Genomic Activity

    Daisuke Sawada, Tomoyuki Katayama, Yuya Tsukuda, Nozomi Saito, Hiroshi Saito, Ken-ichiro Takagi, Eiji Ochiai, Seiichi Ishizuka, Kazuya Takenouchi, Atsushi Kittaka

    Tetrahedron   66 ( 29 )   5407 - 5423   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    2 alpha- and 2 beta-Substituted analogs of 14-epi-previtamin D-3 were synthesized and isolated after thermal isomerization of 14-epi-vitamin D-3 triene at 80 degrees C. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were tested, and the 2 alpha-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D-3. We found that modification at the C2 position of the seco-steroidal skeleton afforded interesting effects for biological genomic activity for the previtamin D form as well as the natural vitamin D form. (C) 2010 Elsevier Ltd. All rights reserved.

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  • Studies on the Synthesis and Metabolism of 14-epi-2-(3-Hydroxypropyl)-19-norvitamin D3 and Its 2-Isomer

    Atsushi Kittaka, Hideki Hara, Kaori Yasuda, Masashi Takano, Midori A. Arai, Daisuke Sawada, Hiroshi Saito, Kazuya Takenouchi, Tai C. Chen, Toshiyuki Sakaki

    Heterocycles   82 ( 1 )   649 - 661   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    Two derivatives of 14-epi-1 alpha,25-Dihydroxy-19-norvitamin D-3, 14-epi-2 alpha-(3-hydroxypropyl)-1 alpha,25-dihydroxy-19-norvitamin D-3 (14-epi-MART-10) and its 2-epimeric analog (14-epi-MART-11), were synthesized using Julia coupling reaction to connect between the C5 position (steroidal numbering) of an A-ring precursor ketone derived from (-)-quinic acid and the C6 position of a protected 14-epi-CD-ring benzothiazole sulfone. The coupling and deprotection reactions generated a mixture of 14-epi-MART-10 and 14-epi-MART-11 in a moderate yield. The C2-isomers were then separated as their pivalate forms. The C2-stereochemistry of 2 alpha- and 2 beta-isomers was determined by H-1 NMR studies including NOE experiments. The pivaloyl group was removed under basic conditions to obtain the target molecules of 14-epi-MART-10 and 14-epi-MART-11. The metabolism of these two new analogs was further studied in a reconstituted cell-free human CYP24A1 system to elucidate the potential mechanism of their super agonistic action on vitamin D receptor. Our results indicate that epimerization at C14 makes the analogs less susceptible to CYP24A1 degradation and therefore more bio-available, leading to enhanced biological activities.

    DOI: 10.3987/COM-10-S(E)40

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  • Synthesis of 2-Substituted-14-epi-previtamin D3 and Testing of Its Genomic Activity

    Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Ken-ichiro Takagi, Eiji Ochiai, Seiichi Ishizuka, Kazuya Takenouchi, Atsushi Kittaka

    J. Steroid Biochem. Mol. Biol.   121 ( 1-2 )   20 - 24   2010年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    2 beta-Substituted analogs of 14-epi-previtamin D-3 were synthesized for the first time by the thermal isomerization of the corresponding 14-epi-vitamin D-3 that were available using coupling reaction between the A-ring phosphine oxide derived from a chiral epoxide and CD-ring cis-hydrindanone. The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were evaluated, and the new analogs were found to be less active, 0.01-0.18% of VDR binding affinity compared with the natural hormone and EC50 1.0-9.1 nM for transactivation activity, than 14-epi-previtamin D3 with 0.5% (VDR) and EC50 0.46 nM, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.jsbmb.2010.02.035

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  • Revisiting AI-2 Quorum Sensing Inhibitors: Direct Comparison of Alkyl-DPD Analogues and a Natural Product Fimbrolide 査読

    Colin A. Lowery, Takumi Abe, Junguk Park, Lisa M. Eubanks, Daisuke Sawada, Gunnar F. Kaufmann, Kim D. Janda

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   131 ( 43 )   15584 - +   2009年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    Quorum sensing (QS) systems have been discovered in a wide variety of bacteria, and mediate both intra- and interspecies communication. The AI-2-based QS system represents the most studied of these proposed interspecies systems and has been shown to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the study of unknown AI-2-based QS systems and the potential treatment of bacterial infections. The fimbrolide class of natural products has exhibited excellent inhibitory activity against AI-2-based QS and as such may be considered the "gold standard" of AI-2 inhibitors. Thus, we sought to include a fimbrolide as a control compound for our recently developed alkyl-DPD panel of AI-2 modulators. Herein, we present a revised synthesis of a commonly studied fimbrolide as well as a direct comparison between the fimbrolide and alkyl-DPD analogues. We demonstrate that our alkyl-DPD analogues are more potent inhibitors of QS in both Vibrio harveyi and Salmonella typhimurium, the two organisms with defined AI-2 QS systems, and in doing so call into question the widely accepted use of fimbrolide-derived compounds as the "gold standard" of AI-2 inhibition.

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  • Synthesis of 2alpha-substituted-14-epi-previtamin D3 and its genomic activity. 査読

    Sawada D, Katayama T, Tsukuda Y, Saito N, Takano M, Saito H, Takagi K, Ochiai E, Ishizuka S, Takenouchi K, Kittaka A

    Bioorganic & medicinal chemistry letters   19 ( 18 )   5397 - 5400   2009年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    DOI: 10.1016/j.bmcl.2009.07.112

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  • Synthesis and biological activities of 14-epi-MART-10 and 14-epi-MART-11: implications for cancer and osteoporosis treatment. 査読

    Kittaka A, Hara H, Takano M, Sawada D, Arai MA, Takagi K, Chida T, Harada Y, Saito H, Takenouchi K, Ishizuka S, Hayashi K, Ikushiro S, Sakaki T, Sugiura T, Chen TC

    Anticancer research   29 ( 9 )   3563 - 3569   2009年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

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  • Synthesis and Biological Evaluation of 4-Substituted Vitamin D and 14-Epi-Previtamin D Analogs

    Daisuke Sawada, Yuya Tsukuda, Hiroshi Saito, Ken-ichiro Takagi, Kyouhei Horie, Eiji Ochiai, Kazuya Takenouchi, Atsushi Kittaka

    Chem. Pharm. Bull.   57 ( 12 )   1431 - 1433   2009年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PHARMACEUTICAL SOC JAPAN  

    We synthesized the 4-hydroxy and 4-methoxy analogs of active vitamin D, (1 alpha,25(OH)(2)D-3, 1) and its C-14-epimer with the previtamin D-3 form of 14-epi-1 alpha,25(OH)(2)preD(3) (14-epi-pre1). Their vitamin D receptor (VDR) binding affinity and osteocalcin promoter transactivation activity in HOS cells were evaluated, and had lower activity than the natural hormone (1) and 14-epi-pre1, respectively.

    DOI: 10.1248/cpb.57.1431

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  • Novel synthesis of oligosaccharides linked with carbamate and urea bonds utilizing modified Curtius rearrangement 査読

    Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami

    TETRAHEDRON   64 ( 37 )   8780 - 8788   2008年9月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    We describe a novel synthesis of various carbamate- and urea-linked disaccharides stereospecifically using sugar carboxylic acids and sugar alcohols or sugar amines by the modified Curtius rearrangement. In this reaction, the reactivity of each hydroxyl group in glucose as an acceptor has been disclosed. Furthermore. we applied this method to the synthesis of carbamate-linked oligosaccharides including a dendritic molecule. (C) 2008 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tet.2008.06.089

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  • Novel synthesis of carbamate-linked oligosaccharides by a modified curtius rearrangement 査読

    Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2007 ( 7 )   1064 - 1068   2007年2月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    We describe a novel stereospecific synthesis of various carbamate-linked disaccharides using sugar carboxylic acids and sugar alcohols by a modified Curtius rearrangement. Furthermore, we applied this method to the synthesis of carbamate-linked oligosaccharides including a dendritic molecule. (C) Wiley-VCH Verlag GmbH & Co.

    DOI: 10.1002/ejoc.200600993

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  • Short-step synthesis of 5-thio-l-hexopyranoses from d-glyconothio-O-lactones 査読

    Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami

    Heterocycles   66 ( 1 )   441 - 451   2005年12月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)  

    We developed a synthetic method for 5-thio-l-hexopyranose from d-glyconothio-O-lactone using the initial ring-opening reaction and subsequent recyclization under Mitsunobu conditions. Using this method, only a three-step transformation is required from d-glyconothio-O-lactone to 5-thio-l-glyconolactone. © 2005 The Japan Institute of Heterocyclic Chemistry.

    DOI: 10.3987/COM-05-S(K)52

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  • Synthesis of N-protected azaoligosaccharides and their cyclic derivatives 査読

    Daisuke Sawada, Hideyo Takahashi, Moto Shiro, Shiro Ikegami

    Tetrahedron Letters   46 ( 14 )   2399 - 2403   2005年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Elsevier Ltd  

    Azaoligosaccharides are prepared through the glycosylation of nojirimycin derivatives with catalytic amounts of TMSOTf. Also, the 1-6′, 1′-6-cyclic azadisaccharides are successfully synthesized, and their one-pot syntheses are demonstrated. © 2005 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2005.02.057

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  • Efficient synthesis of 1-deoxy-azasugars as useful synthetic tools 査読

    Daisuke Sawada, Hideyo Takahashi, Shiro Ikegami

    Tetrahedron Letters   44 ( 15 )   3085 - 3088   2003年4月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:Elsevier Ltd  

    1-Deoxy-azasugars are efficiently prepared from sugar-lactones using a stereoinversion process and they are applied to the synthesis of a natural product. © 2003 Elsevier Science Ltd. All rights reserved.

    DOI: 10.1016/S0040-4039(03)00512-4

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  • A new method for formacetal linkage formation: Protection of alcohols, phenols and carboxylic acids

    Daisuke Sawada, Yukishige Ito

    Tetrahedron Letters   42 ( 13 )   2501 - 2504   2001年3月

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    掲載種別:研究論文(学術雑誌)  

    A new formacetal linkage (ROCH2OR′) forming reaction was developed, which exploited a combination of sulfide (R′OCH2SR″) and CuBr2-Bu4NBr. This reaction proceeded to give high yields under neutral conditions and was applied to the protection of alcohols, phenols and carboxylic acids by several types of α-oxymethyl groups. © 2001 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4039(01)00212-X

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  • Enantioselective total synthesis of epothilones A and B using multifunctional asymmetric catalysis 査読

    D Sawada, M Kanai, M Shibasaki

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   122 ( 43 )   10521 - 10532   2000年11月

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:AMER CHEMICAL SOC  

    An enantioselective total synthesis of epothilones A (1) and B (2) using multifunctional asymmetric catalysis such as a cyanosilylation of an aldehyde, an aldol reaction of an unmodified ketone with an aldehyde, and a protonation in the conjugate addition of a thiol to an alpha,beta -unsaturated thioester has been achieved. We divided 1 and 2 into fragment A, fragment B, and fragment C. A catalytic asymmetric synthesis of fragments A and B was accomplished using a catalytic asymmetric cyanosilylation as a key step. An enantiocontrolled synthesis of fragment C was achieved in two ways. One is the use of a direct catalytic asymmetric aldol reaction of an unmodified ketone with an aldehyde as a key step, and the other utilizes a catalytic asymmetric protonation in the conjugate addition of a thiol to an alpha,beta -unsaturated thioester as a key step. Suzuki cross-coupling of fragment A with fragment C followed by Yamaguchi lactonization as key steps led to an enantiocontrolled synthesis of epothilone A (1). On the other hand, Suzuki cross-coupling of fragment B with fragment C followed by Yamaguchi lactonization accomplished an enantiocontrolled synthesis of epothilone B (2).

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  • Enantioselective total synthesis of epothilone A using multifunctional asymmetric catalyses 査読

    D Sawada, M Shibasaki

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   39 ( 1 )   209 - +   2000年

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    記述言語:英語   掲載種別:研究論文(学術雑誌)   出版者・発行元:WILEY-V C H VERLAG GMBH  

    A catalytic version has now been developed for the enantioselective total synthesis of epothilone A (1). The key is the use of multifunctional asymmetric catalySes for a direct aldol reaction and cyanosilylation. This successful approach demonstrated the usefulness of these reactions for the catalytic asymmetric synthesis of complex molecules.

    DOI: 10.1002/(SICI)1521-3773(20000103)39:1<209::AID-ANIE209>3.0.CO;2-F

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  • A new bifunctional asymmetric catalysis: An efficient catalytic asymmetric cyanosilylation of aldehydes 査読

    Y Hamashima, D Sawada, M Kanai, M Shibasaki

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   121 ( 11 )   2641 - 2642   1999年3月

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    記述言語:英語   出版者・発行元:AMER CHEMICAL SOC  

    DOI: 10.1021/ja983895c

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  • Novel phorbol analogs which bind to protein kinase C (PKC) without activation

    K. Sugita, D. Sawada, M. Sodeoka, H. Sasai, M. Shibasaki

    Chemical and Pharmaceutical Bulletin   44 ( 2 )   463 - 465   1996年

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    掲載種別:研究論文(学術雑誌)  

    13-Deacetoxy-11-demethyl-phorbol derivatives with acyl groups of various lengths (from hexanoyl to tetradecanoyl) at the C-12 position were synthesized in an optically active form. Although considerable binding affinities to PKC were observed by analogs 3-7, no activation of PKC was seen even at 10 μM.

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▼全件表示

MISC

  • Development of chromic molecule that can change color and absorption/fluorescence wavelengths largely in response to external stimuli

    Shinichiro Kamino, Masaru Tanioka, Daisuke Sawada

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry   76 ( 10 )   1066 - 1075   2018年

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    掲載種別:書評論文,書評,文献紹介等  

    Aminobenzopyranoxanthene (ABPX) dye, developed by our group, exhibits two-step color change in solution through a spiro-ring opening/closing process in response to chemical stimuli such as acids, metal ions and phenols. Using this unique characteristic, we have developed ABPX-based colorimetric sensor that change color depending on Cu2+ concentration, enabling visualization by spectrophotometry and the naked eye. Furthermore, an efficient and practical method to prepare ABPX with various nitrogen-containing fused rings was developed. Using a simple acid-catalyzed reaction consisting of 1,3-diisopropoxybenzene and CH 3SO 3H, a variety of benzophenones gave ABPX directly in excellent yields. We discovered that ABPX is a new type of mechanochromic organic molecule with a large wavelength difference of fluorescence (near-IR/blue). Detailed spectrophotometric and single-crystal X-ray analyses revealed that the near-IR fluorescence is attributable to fluorescence from slip-stacked dimeric structures in crystals, while the blue fluorescence is attributable to fluorescence from the monomer. Switching between the two is achieved by dynamic structural interconversion in response to mechanical grinding and exposure to the vapor of solvents.

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  • 8,9‐ジヒドロ‐19‐ノルタキステロール誘導体の合成と生物活性評価

    松本洋太郎, 澤田大介, 竹内明子, 橘高敦史

    反応と合成の進歩シンポジウム講演要旨集   40th   27   2014年10月

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  • 8,9‐ジヒドロ‐19‐ノルタキステロールの合成研究

    松本洋太郎, 山田徹, 森幸樹, 澤田大介, 橘高敦史

    日本薬学会関東支部大会講演要旨集   58th   189   2014年9月

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  • 2-II-19 2α位にテトラゾールプロピル基を有する19-ノル型ビタミンD_3の合成と生物活性評価(一般演題要旨,第66回大会講演要旨)

    高野 真史, 樋口 恵理香, 竹内 明子, 澤田 大介, 橘高 敦史

    ビタミン   88 ( 4 )   244 - 244   2014年4月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • 14‐エピ‐8,9‐ジヒドロ‐1α,25‐ジヒドロキシ‐19‐ノルタキステロールの合成

    澤田大介, 松本洋太郎, 竹内明子, 橘高敦史

    日本薬学会年会要旨集(CD-ROM)   134th   ROMBUNNO.29AMS-054   2014年

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  • 2. 2α-アゾールエチル基を有する1α, 25-ジヒドロキシビタミンD_3の合成と生物活性評価(研究発表,第340回会議研究発表要旨,脂溶性ビタミン総合研究委員会)

    橘高 敦史, 堀江 恭平, 上村 みどり, 竹之内 一弥, 松尾 実紀, 長谷川 麻美, 高野 真史, 澤田 大介, 齋藤 博, 角田 真二, 高木 健一郎, 落合 鋭士

    ビタミン   87 ( 11 )   2013年

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    記述言語:日本語   出版者・発行元:公益社団法人 日本ビタミン学会  

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  • 2-III-6 14-エピタキステロール類の合成とVDR結合様式の解明(一般演題要旨,第65回大会講演要旨)

    澤田 大介, 堀江 恭平, 落合 鋭士, 竹内 明子, 角田 真二, 上村 みどり, 橘高 敦史

    ビタミン   87 ( 4 )   2013年

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    記述言語:日本語   出版者・発行元:公益社団法人 日本ビタミン学会  

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  • 2alpha-(3-ヒドロキシプロピル)-lalpha,25-ジヒドロキシ-19-ノルビタミンD_3(MART-10)とその類縁体の合成と抗がん活性等(研究発表,第336回会議研究発表要旨,脂溶性ビタミン総合研究委員会)

    高野 真史, 澤田 大介, 橘高 敦史, 高木 健一郎, 千田 貴之, 原田 善文, 齋藤 博, 山本 恵子, 榊 利之, Chiang Kun-Chun, Zheng Shasha, Flanagan John N, Chen Tai C

    ビタミン   86 ( 12 )   694 - 696   2012年12月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

    DOI: 10.20632/vso.86.12_694

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  • ヒト由来CYP24A1抵抗性ビタミンD誘導体合成とATRA耐性APL細胞分化誘導(一般演題要旨,日本ビタミン学会第64回大会講演要旨)

    高野 真史, 松本 直樹, 林 恵子, 生城 真一, 榊 利之, 角田 真二, 高木 健一郎, 落合 鋭士, 堀江 恭平, 上村 みどり, 澤田 大介, 野尻 久雄, 橘高 敦史

    ビタミン   86 ( 4 )   2012年4月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • 14-エピ-19-ノルタキステロールの合成とVDRリガンド骨格としての可能性(第332回会議研究発表要旨,脂溶性ビタミン総合研究委員会)

    澤田 大介, 佃 勇也, 橘高 敦史, 齋藤 博, 角田 真二, 上村 みどり, 竹之内 一弥

    ビタミン   86 ( 3 )   181 - 182   2012年3月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

    DOI: 10.20632/vso.86.3_181

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  • EVALUATION AND CHARACTERIZATION OF 14-EPI-19-NORTACHYSTEROL ANALOGS FROM 14-EPI-19-NORPREVITAMIN D-3

    D. Sawada, Y. Tsukuda, H. Saito, K. Takagi, S. Kakuda, M. T. Kamimura, K. Takenouchi, A. Kittaka

    ANTICANCER RESEARCH   31 ( 4 )   1501 - 1501   2011年4月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:INT INST ANTICANCER RESEARCH  

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  • SYNTHESIS OF C15-MODIFIED 16-ENE-ACTIVE VITAMIN D-3 ANALOGS FOR THE RECEPTOR-LIGAND INTERACTION STUDIES

    A. Kittaka, G. Kumagai, M. Takano, D. Sawada, H. Saito, S. Kakuda, K. Takagi, E. Ochiai, K. Horie, K. Takenouchi, M. T. Kamimura, T. C. Chen

    ANTICANCER RESEARCH   31 ( 4 )   1500 - 1501   2011年4月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:INT INST ANTICANCER RESEARCH  

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  • 変異VDR(Arg274Leu)に対するセコステロイドリガンドの設計と合成(第329回会議研究発表要旨,脂溶性ビタミン総合研究委員会)

    本澤 忍, 高橋 尚志, 山本 康弘, 荒井 緑, 高野 真史, 澤田 大介, 山下 純, 杉浦 隆之, 橘高 敦史, 角田 真二, 齋藤 博, 高木 健一郎, 上村 みどり, 石塚 誠一, 竹之内 一弥, 榊 利之, 加藤 茂明, 栗原 正明

    ビタミン   85 ( 3 )   166 - 167   2011年3月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

    DOI: 10.20632/vso.85.3_166_2

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  • 2-II-20 2α位にアゾール環側鎖を有する活性型ビタミンD_3の合成と生物活性評価(一般演題要旨,日本ビタミン学会第63回大会講演要旨)

    高野 真史, 上村 みどり, 竹之 内一弥, 澤田 大介, 橘高 敦史, 松尾 実紀, 長谷川 麻美, 中村 優子, 齋藤 博, 角田 真二, 高木 健一郎, 落合 鋭士, 堀江 恭平

    ビタミン   85 ( 4 )   2011年

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    記述言語:日本語   出版者・発行元:公益社団法人 日本ビタミン学会  

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  • 1-I-6 新規15位置換活性型ビタミンD_3の合成研究(一般演題,日本ビタミン学会第62回大会発表要旨)

    熊谷 剛, 上村 みどり, 竹之内 一弥, 橘高 敦史, 澤田 大介, 新藤 香菜子, 高野 真史, 角田 真二, 齋藤 博, 高木 健一郎, 落合 鋭士, 堀江 恭平

    ビタミン   84 ( 4 )   2010年

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  • 1-I-5 14-epi-19-norprevitamin D_3から14-epi-19-nortachysterolへの展開(一般演題,日本ビタミン学会第62回大会発表要旨)

    澤田 大介, 佃 勇也, 堀江 恭平, 落合 鋭士, 齋藤 博, 角田 真二, 上村 みどり, 竹之内 一弥, 橘高 敦史

    ビタミン   84 ( 4 )   2010年

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  • 1-I-7 2α位に2-(1H-テトラゾール-1-イル)エチル基及び 2-(2H-テトラゾール-2-イル)エチル基を有する活性型ビタミンD_3の合成と生物活性評価(一般演題,日本ビタミン学会第62回大会発表要旨)

    松尾 実紀, 上村 みどり, 竹之内 一弥, 澤田 大介, 橘高 敦史, 長谷川 麻美, 高野 真史, 中村 優子, 齋藤 博, 角田 真二, 高木 健一郎, 落合 鋭士, 堀江 恭平

    ビタミン   84 ( 4 )   2010年

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  • 新規15位置換活性型ビタミンD3の合成とビタミンD受容体との相互作用および生物活性(第324回脂溶性ビタミン総合研究委員会研究発表要旨)

    新藤 香菜子, 高野 真史, 齋藤 望, 澤田 大介, 橘高 敦史, 角田 真二, 齋藤 博, 高木 健一郎, 上村 みどり, 石塚 誠一, 竹之内 一弥

    ビタミン   83 ( 10 )   2009年10月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

    DOI: 10.20632/vso.83.10_593_1

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  • 活性型ビタミンD3の2α位の構造修飾とVDRリガンド結合領域に存在する水分子(water channel)との相互作用と生物活性(第321回会議研究発表要旨,脂溶性ビタミン総合研究委員会)

    高野 真史, 澤田 大介, 橘高 敦史, 杉浦 隆之, 高木 健一郎, 石塚 誠一, 竹之内 一弥, 角田 真二, 上村 みどり, 林 恵子, 生城 真一, 榊 利之

    ビタミン   83 ( 5 )   328 - 329   2009年6月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • 活性型ビタミンD3誘導体における核内受容体Water Channelの維持と生物活性(一般研究発表,日本ビタミン学会第61回大会研究発表要旨)

    高野 真史, 澤田 大介, 林 恵子, 生城 真一, 榊 利之, 角田 真二, 高木 健一郎, 堀江 恭平, 上村 みどり, 竹之内 一弥, 杉浦 隆之, 野尻 久雄, 橘高 敦史

    ビタミン   83 ( 4 )   2009年4月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • MEDI 428-New vitamin D3 analogs: 2alpha-(2,3-Dihydroxypropoxy)- and 2alpha-(2-hydroxypropoxy)- active vitamin D3 with highly potent VDR agonism

    Masashi Takano, Daisuke Sawada, Keiko Hayashi, Shin-ichi Ikushiro, Toshiyuki Sakaki, Ken-ichiro Takagi, Seiichi Ishizuka, Midori Takimoto-Kamimura, Maiko Gokoh, Takayuki Sugiura, Atsushi Kittaka

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   236   2008年8月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:AMER CHEMICAL SOC  

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  • MEDI 87-Synthesis and biological evaluation of novel 2-substituted 14-epi-previtamin D3 analogs

    Daisuke Sawada, Yuya Tsukuda, Nozomi Saito, Tomoyuki Katayama, Hiroshi Saito, Ken-ichiro Takagi, Kazuya Takenouchi, Seiichi Ishizuka, Midori Takimoto-Kamimura, Masashi Takano, Atsushi Kittaka

    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY   236   2008年8月

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)   出版者・発行元:AMER CHEMICAL SOC  

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  • 2位置換14-エピプレビタミンD3誘導体の合成と活性評価(一般研究発表,新世紀ビタミン学の展望と先進的展開を目指して,日本ビタミン学会第60回大会発表要旨)

    澤田 大介, 佃 勇也, 片山 智之, 齋藤 望, 齋藤 博, 竹之内 一弥, 高木 健一郎, 滑川 淳一, 石塚 誠一, 橘高 敦史

    ビタミン   82 ( 4 )   2008年4月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • 14-エピプレビタミンD3への4位置換基の導入(一般研究発表,新世紀ビタミン学の展望と先進的展開を目指して,日本ビタミン学会第60回大会発表要旨)

    佃 勇也, 澤田 大介, 高木 健一郎, 石塚 誠一, 橘高 敦史

    ビタミン   82 ( 4 )   2008年4月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • 2α-(2-Hydroxypropoxy)-1α,25-dihydroxyvitamin D_3の合成と生物活性評価(一般研究発表,新世紀ビタミン学の展望と先進的展開を目指して,日本ビタミン学会第60回大会発表要旨)

    高野 真史, 澤田 大介, 林 恵子, 生城 真一, 榊 利之, 高木 健一郎, 石塚 誠一, 杉浦 隆之, 橘高 敦史

    ビタミン   82 ( 4 )   2008年4月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • Vitamin D hormone: structural refinement of the seco-steroidal skeleton and the nuclear receptor mediated biological activity

    Atsushi Kittaka, Daisuke Sawada, Masashi Takano, Nozomi Saito, Tomoyuki Katayama, Kanako Shindo, Yuya Tsukuda, Shinobu Honzawa, Midori A. Arai, Hiroshi Saito, Ken-ichiro Takagi, Kazuya Takenouchi, Seiichi Ishizuka, Toshiyuki Sakaki, Tai C. Chen

    Anticancer Res.   28 ( 3A )   1618 - 1619   2008年

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    記述言語:英語   掲載種別:研究発表ペーパー・要旨(国際会議)  

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  • A環修飾14-epi-ビタミンD3と14-epi-19-ノルビタミンD3誘導体の合成と生物活性(第316回脂溶性ビタミン総合研究委員会発表要旨)

    澤田 大介, 齋藤 望, 片山 智之, 佃 勇也, 原 英己, 高野 真史, 橘高 敦史, 齋藤 博, 高木 健一郎, 千田 貴之, 原田 善史, 竹之内 一弥, 上村 みどり, 石塚 誠一, Chen Tai C

    ビタミン   81 ( 11 )   582 - 583   2007年11月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

    DOI: 10.20632/vso.81.11_582

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  • 2α-(2, 3-Dihydroxypropoxy)-1α,25-dihydroxyvitamin D3の合成と生物活性評価(ビタミン学の原点・栄養学への21世紀的回帰, 日本ビタミン学会第59回大会)

    高野 真史, 澤田 大介, 林 恵子, 生城 真一, 榊 利之, 高木 健一郎, 石塚 誠一, 岸本 成史, 杉浦 隆之, 橘高 敦史

    ビタミン   81 ( 4 )   2007年4月

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    記述言語:日本語   出版者・発行元:日本ビタミン学会  

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  • A new and facile synthesis of carbamate- and urea-linked glycoconjugate using modified Curtius rearrangement

    Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami

    TETRAHEDRON LETTERS   47 ( 40 )   7219 - 7223   2006年10月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    We describe a facile synthetic method of carbamate- and urea-linked glycoconjugates using sugar carboxylic acids by the modified Curtius rearrangement. This reaction is a simple one-pot procedure, and various nucleophiles including tertiary alcohols can be utilized to afford desired compounds in moderate to high yields. And the stereospecific synthesis of the anomeric isomers is achieved using the corresponding two stereoisomers of glycosyl carboxylic acid. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.07.139

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  • A new and facile synthesis of carbamate- and urea-linked glycoconjugate using modified Curtius rearrangement

    Daisuke Sawada, Shinya Sasayama, Hideyo Takahashi, Shiro Ikegami

    TETRAHEDRON LETTERS   47 ( 40 )   7219 - 7223   2006年10月

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    記述言語:英語   出版者・発行元:PERGAMON-ELSEVIER SCIENCE LTD  

    We describe a facile synthetic method of carbamate- and urea-linked glycoconjugates using sugar carboxylic acids by the modified Curtius rearrangement. This reaction is a simple one-pot procedure, and various nucleophiles including tertiary alcohols can be utilized to afford desired compounds in moderate to high yields. And the stereospecific synthesis of the anomeric isomers is achieved using the corresponding two stereoisomers of glycosyl carboxylic acid. (c) 2006 Elsevier Ltd. All rights reserved.

    DOI: 10.1016/j.tetlet.2006.07.139

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  • Divergent synthesis of (L)-sugars and (L)-iminosugars from D-sugars

    Hideyo Takahashi, Tomomi Shida, Yuko Hitomi, Yoshinori Iwai, Namisa Miyama, Kazusa Nishiyama, Daisuke Sawada, Shiro Ikegami

    CHEMISTRY-A EUROPEAN JOURNAL   12 ( 22 )   5868 - 5877   2006年7月

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    記述言語:英語   出版者・発行元:WILEY-V C H VERLAG GMBH  

    An efficient divergent synthesis Of L-sugars and L-iminosugars from D-sugars is described. The important intermediate, delta-hydroxyalkoxamate, prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxime compound and the N-cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O-/N-cyclization of the delta-hydroxyalkoxamate. Suitable protection at the delta-position of 6-hydroxyalkoxamate, derived from D-glucono-1,5-lactone, afforded the corresponding delta-alkylation product alone. Thus we succeeded in applying this to the total synthesis of L-iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D-glucono/galactono-1,5-lactone into the corresponding L-iminosugars (L-idonolactam and L-altronolactam) was achieved.

    DOI: 10.1002/chem.200600268

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  • Divergent synthesis of (L)-sugars and (L)-iminosugars from D-sugars

    Hideyo Takahashi, Tomomi Shida, Yuko Hitomi, Yoshinori Iwai, Namisa Miyama, Kazusa Nishiyama, Daisuke Sawada, Shiro Ikegami

    CHEMISTRY-A EUROPEAN JOURNAL   12 ( 22 )   5868 - 5877   2006年7月

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    記述言語:英語   出版者・発行元:WILEY-V C H VERLAG GMBH  

    An efficient divergent synthesis Of L-sugars and L-iminosugars from D-sugars is described. The important intermediate, delta-hydroxyalkoxamate, prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxime compound and the N-cyclized lactam compound as mixtures. A more detailed investigation revealed that the appropriate protecting groups and solvents controlled the specificity for the O-/N-cyclization of the delta-hydroxyalkoxamate. Suitable protection at the delta-position of 6-hydroxyalkoxamate, derived from D-glucono-1,5-lactone, afforded the corresponding delta-alkylation product alone. Thus we succeeded in applying this to the total synthesis of L-iduronic acid. In contrast, with both TBDMS as the protecting group and RCN as the solvent the efficient conversion of D-glucono/galactono-1,5-lactone into the corresponding L-iminosugars (L-idonolactam and L-altronolactam) was achieved.

    DOI: 10.1002/chem.200600268

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  • Highly enantioselective cyanosilylation of aldehydes catalyzed by a Lewis acid-Lewis base bifunctional catalyst

    Yoshitaka Hamashima, Daisuke Sawada, Hiroyuki Nogami, Motomu Kanai, Masakatsu Shibasaki

    Tetrahedron   57 ( 5 )   805 - 814   2001年1月

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    A new bifunctional asymmetric catalyst containing a Lewis acid and a Lewis base (1) was developed and applied to the catalytic asymmetric cyanosilylation of aldehydes. The products were obtained generally with excellent enantiomeric excess. The experiments using the control catalyst (5) and the catalyst containing more electron-rich phosphine oxide (6) suggest that the catalyst 1 should promote the reaction via a dual activation of the aldehyde by the aluminum and TMSCN by the phosphine oxide. This reaction is practical and was applied to the catalytic asymmetric total synthesis of epothilone A. © 2001 Elsevier Science Ltd.

    DOI: 10.1016/S0040-4020(00)01039-5

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  • 分子構造解析学 (2020年度) 第1学期  - 月1,月2

  • 創薬化学 (2020年度) 第3学期  - 金5,金6

  • 医薬品構造解析学 (2020年度) 1~4学期  - [第1学期]月1,月2, [第2学期]その他, [第3学期]その他, [第4学期]火3,火4

  • 有機化学・天然物化学 (2020年度) 特別  - その他

  • 有機化学3 (2020年度) 第3学期  - 水1,水2

  • 有機化学3 (2020年度) 第3学期  - 水1,水2

  • 有機化学4 (2020年度) 第4学期  - 水3,水4

  • 有機化学4 (2020年度) 第4学期  - 水3,水4

  • 有機化学III (2020年度) 3・4学期  - 水1,水2

  • 有機合成反応論 (2020年度) 第4学期  - 木5,木6

  • 有機合成反応論 (2020年度) 第4学期  - 木5,木6

  • 精密合成設計学 (2020年度) 特別  - その他

  • 精密合成設計学演習 (2020年度) 特別  - その他

  • 薬学基礎実習Ⅱ (2020年度) 特別  - その他

  • 薬学基礎実習Ⅱ (2020年度) 特別  - その他

▼全件表示